Vacation rentals in Ridgely

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Halcyon house. Lovely views on MD eastern shore.

This charming apartment is located on the Chester river on Maryland's Eastern Shore. The wildlife is abundant and generally very active. The sun rise and sunsets can be spectacular. The property is 20 minutes from Annapolis and 50 minutes from DC. The newly renovated apartment has all new appliances and a well stocked kitchen with many herbs and spices, condiments, coffee, tea, cream and sugar etc. The 8 mile long Cross Island Trail starts a block from the house and leads to several restaurant

Turnbridge Manor - Waterfront Historic House

A waterfront property located in the heart of downtown Denton, on Maryland's Eastern Shore, the stately historic home built in the 1860’s offers modern amenities and luxurious accommodations. Guests can take in the charm of Denton from our sunny front porch or sit in the many outdoor oases to relax and enjoy the beautiful terraced grounds overlooking the tranquil Choptank River. Located less than 60 minutes to the beach, 35 minutes to historic St. Michaels and minutes to the Harriet Tubman Byway

Cheerful & Spacious Shore Life Beauty!

Welcome to our charming yet peaceful abode & island oasis where sailing, marine life, & bay exploration exceed the standard! This exceptional home is conveniently located to a variety of high quality restaurants, parks, outdoor activities, spas, beaches, wedding venues, & other entertainment including live music, hunting, & antiquing while also being 20-minutes from Annapolis & 1-hour from Baltimore City & DC. Let this be your definitive choice for a magical destination you'll forever remember.

River House on the Choptank

Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Guest Suite with Private Entrance

My wife Justine and I are pleased to host this guest suite with private secure entrance and private bathroom. We do live in the main part of the house full time so you may hear us rattling around from time to time and coming and going or working in the yard but most of our time is spent at the opposite end of the house. The room is completely private and inaccessible from the main house. The screened in porch is shared with the main house. We do not currently have WiFi access in the Airbnb.

Home away from Home in Dover DE

Spacious 4-Bedroom Home with Backyard, Game Room & Great Location! Welcome to your home away from home! This comfortable and spacious house offers everything you need for a relaxing stay. It features 4 cozy bedrooms, 2 full bathrooms, a fully equipped kitchen, a welcoming living room that turns into a sofa bed, and a fun basement with a pool table, perfect for relaxing or spending time with family and friends. Enjoy the backyard with a BBQ grill for outdoor meals and quality time.

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

Family Retreat at Historic Lansdowne Manor

Escape to Lansdowne, a historic Federal-period manor house recognized by the Library of Congress. This private, tranquil retreat offers a unique blend of vintage charm and modern comfort for up to 8 guests. Surrounded by open fields and nature, this 4 bedroom home features a fully equipped kitchen and high-speed Wi-Fi. Perfect for families and history lovers seeking a peaceful getaway just minutes from Centreville and a state park lake and trails.

Private bungalow with fire pit near Easton, Denton

- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.